Isopropyl iodide → HCID 86723675, compound

HRID 577436Notes

Reaction equation

HRID 577436 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:10])[CH:5]=[C:6]([Br:9])[C:7]=1[CH3:8].I[CH:12]([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:10][CH:12]([CH3:14])[CH3:13])[CH:5]=[C:6]([Br:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 554573,5-Dibromo-4-methylphenol

Product 1

HCID 86723675HCID 86723675, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3,5-dibromo-4-methyl-phenol (11.2 g, 42.1 mmol), 2-iodopropane (8.50 mL, 85.0 mmol), potassium carbonate (17.5 g, 126 mmol), and anhydrous DMF (100 mL) was stirred at 80° C. for 3 hours. After cooling to room temperature, the reaction mixture was partitioned between ether (300 mL) and water (300 mL). The organic phase was separated, washed with brine (2×300 mL), dried over sodium sulfate, and concentrated under vacuum to give 1,3-dibromo-5-isopropoxy-2-methyl-benzene (Cpd A, 12.8 g, 99% yield) as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe reaction mixture was partitioned between ether (300 mL) and water (300 mL)
  3. customThe organic phase was separated
  4. washwashed with brine (2×300 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-16572f09091b4504bf5965c970031b3b
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

Loading…